Document Detail

New phototriggers: extending the p-hydroxyphenacyl pi-pi absorption range.
MedLine Citation:
PMID:  10841475     Owner:  NLM     Status:  MEDLINE    
[equation--see text] Introducing 3-methoxy or 3,5-dimethoxy substituents on the 4-hydroxyphenacyl (pHP) photoremovable protecting group has been explored with two excitatory gamma-amino acids, L-glutamic acid and gamma-amino butyric acid (GABA). These substituents significantly extend the absorption range of the pHP chromophore, e.g., the tail of absorption bands of 2a,b extend above 400 nm, well beyond the absorptions of aromatic amino acids and nucleotides. Irradiation releases the amino acids with rate constants of approximately 10(7) s(-)(1) and appearance efficiencies (Phi(app)) of 0.03-0.04. The photoproducts are formed through the pHP excited triplet and are primarily products of photoreduction and photohydrolysis. 1a,b also rearranged to the phenylacetic acid 3.
P G Conrad; R S Givens; J F Weber; K Kandler
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Organic letters     Volume:  2     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2000 Jun 
Date Detail:
Created Date:  2000-07-07     Completed Date:  2000-07-07     Revised Date:  2014-05-09    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1545-7     Citation Subset:  IM    
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MeSH Terms
Acetophenones / chemistry,  radiation effects
Bicuculline / pharmacology
Electric Conductivity
Glutamic Acid / chemistry,  pharmacology,  radiation effects
Hippocampus / cytology
Ion Channels / drug effects
Luminescent Measurements
Neurons / drug effects,  physiology,  radiation effects
gamma-Aminobutyric Acid / chemistry,  pharmacology,  radiation effects
Grant Support
Reg. No./Substance:
0/Acetophenones; 0/Ion Channels; 3KX376GY7L/Glutamic Acid; 56-12-2/gamma-Aminobutyric Acid; Y37615DVKC/Bicuculline

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